Skip to main content

Managing the Challenging Person: Tips and Tricks

Tips for dealing with difficult people in the office.

Tips for dealing with difficult people in the office.

Into each life, a difficult individual–or individuals–must fall. Yes, as long as there are two people in a room, the chances of running into a challenging person are rife. Whether it is at work, at play, or in the most tenacious case scenario–within your own family, an erratic person is bound to be a feature.

So, how do we manage relationships with such people, especially if they move within the same social circles or are our immediate family members? While there's no foolproof way to have plain-sailing relationships, we can do our best to make them easier.

10 Types of Challenging Individuals

People are a challenge, including ourselves - we must admit that we bear the traits of the problematic individual. Each of us has any of these traits, to a greater or lesser degree. You'd recognize them in the colleagues or people on the street you meet each day. And recognition is the first step to dealing with problems or challenging individuals.

1. The Know-It Alls

These people are annoying because of their egocentricity and need for one-upmanship. They must always know better than you how to raise children, cook, manage pets, perform a job - just name it, and they'll need to prove that they can do it better. They must always add to conversations and comment that they, too, have experienced this, that, or the other.

2. The Interrupters

These people don't allow you to have your say, either out of a feeling of enthusiasm for the topic or, what is most likely, fear that their voices will not be heard. You will feel their tendency to refuse to let you participate fully in any conversation incredibly grating.

3. The Selectors

These folks choose who they want to befriend and acknowledge. Don't be surprised if you're not among the chosen few - they make being part of their circle almost impossible. Don't take their ignoring personally.

4. The Bore

These people aren't dull per's that they delight in harping on topics that pique their interest, much like a broken record, to the point that they don't realize that the attention of others is waning. Bores are harmless but can prevent you from moving forward with your activities.

5. The Prima Donna

The Prima Donnas are the perfect description of egoism. Everything is about them - their convenience, their needs, their victories, their efforts. Their need for 'me' can seriously undermine success efforts.

6. The Work Martyr

These people never stop working or talking about it. Work is their identity, so they grab the credit for having done some work whenever they can. They also expect you to share their ethos, so do work as hard as they do if you want some way to connect with them. And yes, they do expect gratitude for their effort.

7. The Whiner

These people never stop finding fault with the world around them. Everything is a bottomless pit that they can never climb out of. The negativity that surrounds them wherever they go is overwhelming. they can never climb out of. The negativity that surrounds them wherever they go is overwhelming.

8. The Negativity Spreader

These folks don't find it enough to feel down-they must make sure everyone feels the same way. Passing the negativity around makes it easier to cope with.

9. The Rainmaker

We all know the favourite in the office. He is by no means exceptionally talented, but everybody has to put up with the way they do their work simply because superiors like it. It doesn't matter if the methods are questionable!

10. The Boundary Crosser

Do you remember the famous Atari game Space Invaders? These folks are aliens seeking new worlds. They are not afraid to cross boundaries or invade your space. They will trespass on you in unsettling ways.

Boundary crossers do not care about your wants, needs, or comforts.

Boundary crossers do not care about your wants, needs, or comforts.

My Experiences Dealing with Difficult Colleagues

In each workplace, one or a combination of these challenging folks must be. I have met my fair share of them as a teacher - and I dare say that I am not the only one.

X was a Know-It-All who always had to prove that her lesson plans were better than others on the teaching staff. She would deliberately put herself in the position to mentor other younger colleagues and shut everyone else out so that they would not interfere with what she was doing.

Managing difficult people is more challenging when they are your relatives. I have close relations with no filter. the concept of boundaries eludes them, so they assume that your space is theirs. Of course, contradicting them is quite a task because denying their presence is near impossible.

Close relations who have no qualms about crossing boundaries cause severe migraines. Mine do not find it out of place to reorganize my fridge, so I have to, with firm kindness, tell them that it is not for them to do.

Then, that are friends who behave like Prima Donnas - they cannot allow anyone to outshine them. Mine condescend towards anyone they perceive as less talented or intelligent than they are. The behaviour can quickly descend to a level of ugly one-upmanship. I had an ugly quarrel with a friend whose website simply had to be the best. I grew annoyed with her when she kept fielding critical comments about how to design hers.

Adding to the hostility will create more conflict. Try to stay grounded.

Adding to the hostility will create more conflict. Try to stay grounded.

Dealing with Difficult People

Below are some helpful tactics for dealing with people you find difficult or problematic.

1. Try Loving Kindness

Showing kindness to a challenging individual can be one of the most overwhelming tasks. One's reaction when another person is difficult is to return the favour. That said, a little graciousness takes you further than being confrontational. Situations escalate, and problems remain unsolved when both parties avoid compromise.

I just recently had a sharp word from the friendly neighborhood butcher regarding terms of address. Our parents teach us to address those older than ourselves as "uncle" or "auntie." I addressed the butcher as "uncle"
as a habitual action, forgetting that this is a relatively young man.

The butcher was impolite; he became prickly and chided me for calling him an 'uncle.' But instinct told me not to retaliate. I am contemptuous of being called an auntie myself, so I chose empathy and apologized to him. The graciousness disarmed him, and he stopped bristling. Empathy relieves tension and makes one relatable.

2. Practice Compassion

You have probably heard about how to manage problems. They always move in a circle and somehow return to you. That's because we deny them when we find them overwhelming, only to find that they are trivial compared to what others face.
Such is the reason we should show others a little compassion. You never know what challenges those around you face, and yours probably pale compared to theirs.

3. What Do You Have in Common?

Conversations with difficult people become smoother when you can find something in common with them. commonalities with them. The shed information creates an instant kinship. Conversations with difficult people become smoother when you can find something in common with them. commonalities with them.

4. Share Your Perspective

You'll problems become much easier to solve when you share your perspective of them with others. When you share, you provide the context around the situation and make it easier for them to empathize with you. Your vulnerability will help you connect with them.

5. Don't Shy Away From Conflict

No, no one is asking you to start the fight with the next person you meet. None of us likes to start a quarrel with anybody.

However, conflict seeks us out, whether or not we search for it. This is especially so when there are difficult people involved. There are times when we have to stand up for ourselves and establish boundaries. Surprisingly, conflict can bring benefits; an argument can bring about a resolution when the parties are ready to compromise.

6. Have a Long Gaze at the Person in the Mirror

We can't always point our itchy fingers at angsty people and assume that untoward circumstances are always their fault. Squirm as we may, we sometimes have to take long, hard looks in the mirror and ask what we ourselves have done to mar relationships with the challenging individuals in our lives. Were we demanding or annoying too?

7. Pay Them No Heed

We don't want to come across as being self-righteous. Indeed, we don't want to communicate the notion that we think we are perfect.

What we do want to do is eliminate negativity. Difficult people often provide negative insights, and that can color our perspectives with 50 shades of grey or even black. That's why the best course of action is to ignore them; while change is not a constant with challenging individuals, we do need to protect our mindsets.


Mat Apodaca How to Deal With Difficult People: 10 Expert Techniques

Johnathan Hancock The 10 Most Difficult People

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.